methyl (1R,3S)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-tosyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate | 1443051-68-0

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 哈马拉生物碱
• 英文名称: methyl (1R,3S)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-tosyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate
• CAS: 1443051-68-0
• 化学式: C₂₅H₂₈N₂O₆S
• 分子量: 484.573
• InChiKey: AEKQZHGYFKCUIG-FUDKSRODSA-N

反应信息

• 作为产物：
  描述：

  methyl (3S)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate 、 对甲苯磺酰氯 在 吡啶 、 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 6.17h， 生成 methyl (1R,3S)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-tosyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate 、 methyl (1S,3S)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-tosyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate
  参考文献：
  名称：

  Novel asymmetric total syntheses of (R)-(−)-pyridindolol, (R)-(−)-pyridindolol K1, and (R)-(−)-pyridindolol K2 via a mild one-pot aromatization of N-tosyl-tetrahydro-β-carboline with (S)-2,3-O-isopropylidene-l-glyceraldehyde as the source of chirality

  摘要：

  Novel total syntheses of (R)-(-)-pyridindolol 1, (R)-(-)-pyridindolol K1 2, and (R)-(-)-pyridindolol K2 3 are described. By using L-tryptophan methyl ester and (S)-2,3-O-isopropylidene-L-glyceraldehyde as the starting materials, (R)-(-)-pyridindolol 1, (R)-(-)-pyridindolol K1 2, and (R)-(-)-pyridindolol K2 3 were synthesized in 5-7 steps in 66%, 41%, and 55% overall yields, respectively. The characteristic step of the total syntheses is a mild one-pot aromatization of N-tosyl-1,2,3,4-tetrahydro-beta-carboline (N-Ts-THBC), which was obtained via Pictet-Spengler reaction of L-tryptophan methyl ester with (S)-2,3-O-isopropylidene-L-glyceraldehyde, and subsequent N-tosylation. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.04.009